Methyl iodide → 1,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 450453노트

반응식

HRID 450453 반응식
[CH3:1][C:2]1[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)=[CH:5][NH:4][N:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.CCOC(C)=O>[CH3:16][N:4]1[CH:5]=[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)[C:2]([CH3:1])=[N:3]1.[CH3:16][N:3]1[C:2]([CH3:1])=[C:6]([B:7]2[O:11][C:10]([CH3:13])([CH3:12])[C:9]([CH3:15])([CH3:14])[O:8]2)[CH:5]=[N:4]1

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178434487HCID 178434487, 화합물

생성물 2

HCID 426473131,5-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole수율 166.7%HCID 426473161,3-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.3 g, 1.442 mmol) and potassium carbonate (0.996 g, 7.21 mmol) were suspended in acetonitrile (10 ml) and stirred overnight at RT. Additional iodomethane (0.5 ml) was added and the mixture was stirred overnight at RT. The mixture was diluted with EtOAc and the inorganic salts were removed by filtration. The filtrate was evaporated to yield an inseparable mixture (2:1) of 1,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.267 g, 83% yield). MS (ESI) m/z: 223.1 (M+H+).

후처리

  1. stirringthe mixture was stirred overnight at RT
  2. customthe inorganic salts were removed by filtration
  3. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-58b83968c1d144188f08b04f53ea63ca
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486951B2

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